Riddle Race Graphic


The Ultimate Riddle Race is an exciting competition between thirty teams in Calvert County who are racing to solve puzzles, complete challenge challenges, and collect clues to become the Ultimate Riddlers! At the same time, we are raising crucial funds to support the Crohn's & Colitis Foundation and support the more than 3 million Americans impacted by these diseases. Watch our exciting event trailer here! This year's race is on September 19th, 2020. PLEASE NOTE: Despite the uncertainty surrounding COVID-19 our event will proceed as planned, although changes to certain course obstacles and challenges may occur. In fact, your support and our efforts will be more important than ever this year, and we hope you're ready to race!

No two Ultimate Riddle Races have EVER been alike, and this year's event promises to be our biggest & best race yet!  It would be impossible to quickly sum up the Ultimate Riddle Race, but here's our best shot:

  • Teams compete to solve puzzles, search for clues, complete activities and arrive at the finish before time runs out. At the end of the race, we celebrate with a great party – food, adult beverages, live entertainment, raffles, and of course prizes for our winning and most spirited teams.
  • I can solve puzzles, but I’m not sure about the challenges….No bungee jumping, but you may have to recite a poem, run a gentle obstacle course, move marshmallows on a straw or take a short trip in a kayak. Not all members of a team perform all challenges, so it is possible to get through without doing anything physical.
  • Teams receive their Riddle Book at the start of the race. The riddles may be in the form of riddles, puzzles or something completely different. All Riddle sites are within Calvert County. The Riddle Book contains valuable information to solve puzzles. Pay attention! Anything could be a hint!


One team captain should click "Form a Team" on this webpage. During the registration process, you may register additional teammates, or you can share your team page and have others join you at another time. Each riddler is $50 and includes a Riddle Race t-shirt, after party dinner, door prize tickets, and all the fun of the Riddle Race! The registration fee will be added to your fundraising webpage to jump start your fundraising efforts! T-shirt sizes and incentives are guaranteed until August 15, so please register as soon as possible. The maximum number of teammates is the maximum legal number of people who can fit in one vehicle (i.e. a 7-person minivan may have 7 total teammates). If you'd like to register more than one team you may do so, however each team must have a different team captain.


While there is NO required fundraising to participate, we are aiming to raise more than $55,000 to support the Crohn's & Colitis Foundation this year! Each riddlers registration will be added to your fundraising webpage to jump start your fundraising efforts! Additionally, as team's raise funds (each participant on a team contributes to the team goal), you have the opportunity to earn important hints & clues during the race that will assist your team -- this includes phone hints, extra Riddle Books, fast passes, and a coveted skip a Riddle option! You have the opportunity to self-donate these amounts during registration, but we also have all the tools you need to easily hit and exceed your fundraising goal, and will be there to help you every step of the way!

NEW THIS YEAR, upon registration, each participant will get their own fundraising webpage that they can customize with photos, their story, and more. There is also BUILT-IN Facebook Fundraising to make it even easier! If you have any questions about the fundraising process, please feel free to reach out to Brett Curtis at bcurtis@crohnscolitisfoundation.org or 646-584-1513.


Grace Picture 1 Grace Picture 2

Our 2020 Ultimate Riddle Race Honored Hero is Grace Campbell! You can learn more about Grace, her story, who she thinks will win this year's race, and more by watching our Facebook Live interview located here. Grace will be sharing more about her story & why she's excited to participate in the Ultimate Riddle Race here shortly, as well as during our event!


We will be hosting one session this year with a maximum of 20 teams be sure to register early to secure your spot!
12:00pm: Team Check-In begins 
1:30pm: The Race begins promptly at 1:30pm. Teams are released in order of most funds raised. 
4:30pm: All team's MUST check-in at the designated check-in point with their completed Riddle Book BEFORE 4:30pm. 
7:00pm-10:00pm: After race party, live concert by SUCKER PUNCH, raffles, door prizes, team prizes & winners announced. After party only tickets will be available for purchase for $25 shortly.
**Our 2020 After Party will be at a NEW LOCATION: The Holiday Inn on Solomons Island

I heard there was a pre-party?? Yes, we will hold an Ultimate Riddle Race Happy Hour for all registered teams approximately two weeks before the event. Please join us for the opportunity to meet other teams and participate in a few mind games! We would like to collect any money you have raised not through your online pages at the Happy Hour and credit it to your team. We believe that will speed up registration on the day of the race. You may continue to raise money up until September 19th! We will collect the balance at registration. (Exact date and location of Pre-Party to be announced)

Take me through a "typical" Riddle Race....There is nothing typical, but you might expect something like this: Your team shows up at the starting location and checks in. Because you raised $455, your team will start somewhere in the middle of the pack. At start time, you receive an envelope with a PHONE HINT (because you raised more than $100) and two RIDDLE BOOKS (because you raised more than $200). You get in your car and immediately begin to look through the RIDDLE BOOK for clues. (There will be approximately 10-12 clues to solve.) Each riddle will lead you to a location in Calvert County. Go there. At each location you will be required to complete a task, i.e. take a picture, audition for a play, try on a frozen t-shirt. Once you have completed the task, you will receive a clue to solve the Ultimate Riddle. You will also get a stamp on the last page of your book and head to your next Riddle location. Solve as many riddles as you can, and get to the finish line before 6 p.m. Teams must check in by 6 p.m. to be eligible to win. The team that solves the most puzzles and completes the most tasks will win. In the event of a tie, the team that arrived at the finish line earlier will be declared the winner.


As our event as grown & changed through the years, we are excited to again offer After-Party tickets this year! If you're not participating in the actual race, but want to attend and join us for appetizers, live entertainment, door prize tickets, and a great concert by SUCKER PUNCH beginning at 7:00pm, you can purchase an after-party ticket here shortly. Tickets are $25.


Team and Individual Fundraising incentives will be available to all players who exceed their fundraising minimum!

Top Fundraising Team

The top fundraising team will be given their Riddle Book and allowed to begin the race before any other team! All teams will be released in the order of final fundraising amounts. If your team raises $204 you will start ahead of a team that raises $203.  THAT MEANS EVERY FUNDRAISING DOLLAR COUNTS!

Skip a Riddle - $1,000 Raised!

Teams that raise $1,000 will get all of the above, PLUS a coveted “SKIP A RIDDLE” pass which will enable them to skip a riddle completely!

Skip a Challenge - $500 Raised!

Teams that raise $500 will get a PHONE HINT, EXTRA RIDDLE BOOK, and SKIP A CHALLENGE pass to skip the challenge once getting to a riddle location!

Extra Riddle Book - $150 Raised!

Teams that raise $150 will get a PHONE HINT and an EXTRA RIDDLE BOOK to facilitate puzzle solving and route planning;

Phone Hint - $50 Raised!

Teams that raise $50 or more will get one PHONE HINT allowing them to call in and ask a question during the race (The question can not be the exact location)


Questions about the Ultimate Riddle Race, event logistics, sponsorship opportunities, volunteering, and day-of experience should be directed to Greg Russell at grussell13@comcast.net

Questions about the Crohn's & Colitis Foundation, registration, website, fundraising support, Facebook integration, and donation methods should be directed to Brett Curtis at bcurtis@crohnscolitisfoundation.org or 646-584-1513. 


The Ultimate Riddle Race is a prime opportunity for you to simultaneously support our mission and showcase your business to a wide array of participants who will be at the event and in locations throughout Calvert County. This unique, team event and race is a county-wide scavenger hunt that draws more than 500 attendees and supporters and, new this year, culminates in an exciting dinner and afterparty with live entertainment, drinks, dancing, raffles, and more! You can view our sponsorship packet and learn more about these opportunies here


  • Minimum of 2 riddlers per team with one team captain. At least one teammate must be 18+. The max number of teammates per team is the maximum number of people legally allowed to fit in ONE vehicle (i.e. a 7-person minivan can have 7 total teammates). If you'd like to register more than one team, you can do so.
  • All team members must travel in a single vehicle throughout the race. Team members must stay together at Riddle sites.
  • You do NOT have to solve the riddles in order.
  • Teams are forbidden from intentionally or unintentionally hindering the performance of other teams IN ANY WAY, i.e. blocking another team’s vehicle, altering a Riddle site, etc..
  • Teams must follow all traffic laws throughout the race. Any team determined to be speeding or driving recklessly will be disqualified.
  • Teams must check in by 4:30 at a designated location with their completed, intact Riddle Book to be eligible to win.
  • All disputes will be resolved by The Ultimate Riddle Race Committee.
  • Great prizes will be awarded to 1st, 2nd and 3rd place teams.
  • Do not cheat. Do not hinder another team. Please do not do anything to ruin the reputation of Calvert Crohn’s, The Crohn’s & Colitis Foundation or this event.  The Ultimate Riddle Race committee reserves the right to modify or add to these rules as needed.
  • A full FAQ will be posted and shared with all teams before the race.
  • Questions about the race? Email Greg Russell at grussell13@comcast.net